Perfect Pairings: Boston & Vermont

United States of America
5 nights private tour from $7,000
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Perfect Pairings Boston Vermont
At a glance
  • Lose yourself in the fascinating history and architecture of Boston with a VIP walking tour of the historic Freedom Trail

  • Stay at Vermont’s most beautiful address – the Woodstock Inn built by the Rockefeller family

  • Be blown away by the beauty and small-town charm of Woodstock – taking in its wholesome wonder and unique character with personally curated private experiences

  • Go wild and adventure through the Winslow state park soaking up the expansive views of the White Mountains

Journey highlights
  • Lose yourself in the fascinating history and architecture of Boston with a VIP walking tour of the historic Freedom Trail

  • Stay at Vermont’s most beautiful address – the Woodstock Inn built by the Rockefeller family

  • Be blown away by the beauty and small-town charm of Woodstock – taking in its wholesome wonder and unique character with personally curated private experiences

  • Go wild and adventure through the Winslow state park soaking up the expansive views of the White Mountains

Our tailor made journeys include:
  • Your dedicated Travel Consultant who will take care of arrangements
  • Private international airport transfers in destination
  • Your own private, English-speaking local guides
  • Unique experiences, hand-picked by our Journeys team
  • Entrance to must-see local sites
  • Dedicated 24/7 team providing in-country support and guidance
  • Complimentary access to My Scott Dunn – industry-leading travel app providing pre-departure information and in-journey support

When to visit

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Best time to visit
Good time to visit
Average time to visit

Autumn is Boston's most glorious season, though spring and summer are pleasant as well. These times bring in healthy-sized crowds due to favourable weather and special events. Weather usually remains warm throughout September, while cooler temperatures in October bring out the colourful foliage. Winter lasts too long for most people's tastes, stretching from December to April. During this period, visitors can expect temperatures below freezing and plenty of snow.

The best time to visit Vermont is in late spring, summer and early autumn when Fall brings its glorious colours. Most of Vermont is under snow over the winter period and the ski resorts come alive. Cold spells affect Vermont from the end of October till late Spring.

Your Itinerary

Indulge in New England relishing the iconic delights of Boston and Vermont, as we take you on a bespoke journey pairing these spellbinding regions. We’ve created utterly immersive experiences, guiding you through the iconic Freedom Trail whilst soaking up the Boston ambience before journeying to idyllic Woodstock. Explore its best kept secrets with exclusive access to the Rockefeller mansion, all whilst submerging in luxury retreats with first-class facilities and gourmet delights.

Paul Revere Statue and Old North Church

Your Itinerary

Kick start this exceptional journey arriving at XV Beacon, a hidden gem within an impressive Beaux Arts building tucked away in the exclusive neighbourhood of Beacon Hill. Home to its own outstanding art collection making it a standout in the Boston arts scene. Take some time to settle into this unique boutique hotel, priding itself on oustanding service, with the guest rooms pairing elegance and modern comfort.

Your first experience will take you along the Freedom Trail, on your very own VIP walking tour. An iconic must do whilst in Boston, this private experience will highlight hidden gems and interesting facts steering clear of the crowds, making it a very unique experience. The 2.5-mile road will take you past 16 historically significant sights including the Boston Common, the Massachusetts State House, Granary Burying Ground, arriving at Old North Church for an immersive experience. You will then have time at leisure to explore Boston as you wish. Maybe amble the beautiful Acorn Street, or head to Back Bay and indulge in the independent stores on Newbury Street, along with an impressive range of exquisite restaurants and cafes, not forgetting the iconic lobster roll.  Yoiu can then return to the sanctuary of your hotel for an evening meal, with the main restaurant, The Mooo Steakhouse, providing a range of New England cuisine. Try the Lobster Bisque if you get a chance, finishing with a night cap to round off the evening. 


After a delicious breakfast it’s time to bid farewell  as you leave Boston behind and transfer to your next stop, the beautiful quaint town of Woodstock. Your driver will stop at the picturesque Winslow State Park en route for you to stretch your legs and take in the breathtaking mountain views here. Embark on a loop hike to the summit of Mt. Kearsarge to take in expansive views of the White Mountains, Pleasant Lake, and some of central Vermont’s tallest peaks such as Mt. Sunapee and Ragged Mountain.

Woodstock in the Fall - Boston and Vermont

Your Itinerary

Plunge into the heart of Woodstock as you check into its most beautiful address – the Woodstock Inn. The epitome of a grand New England resort, built by the Rockefeller family in the 1960’s, home to heated pools, tennis courts and spa with hot tub nestled in the private walled courtyard. Boasting a prime location, you can head out and browse the unique shops in this beautiful town, like FH Gillingham & Sons general store and the Arts on the Green gallery. Spend time wandering the Main Street with many restaurants and charming boutiques to explore. Heading further afield to the surrounding Green Mountains, an area rich in adventure with its miles of hiking and mountain biking trails. 

The next day we’ve curated a bespoke private tour of Woodstock. Stroll through the iconic village green taking in the town’s unique history and architecture, admiring the restored Georgian, Federal Style and Greek Revival houses as well as local art galleries, and arts and craft stores. You will be given the rare opportunity to take an outside look of the impressive Rockefeller Mansion. Walk Woodstock's beautiful country roads and surrounding farms where you will stop and visit the Billings Farm & Museum, devouring a sublime lunch at the Simon Pearce restaurant. Drive to the Quechee Gorge soaking up the breathtaking view of the valley and Ottauquechee River, its village centre and vintage antique stores. Returning to the wonderful facilities at your hotel for a delicious evening meal in wonderful surroundings. 


Your final experience takes you to a private pottery workshop, where your personal artisan potter will guide you through their fascinating workshop and art collection, demonstrating their exceptional skills and guiding you on the potters wheel, letting you get your hands dirty to create your own masterpiece under their expert eye. 

Itinerary

Day 1-3

Boston

Kick start this exceptional journey arriving at XV Beacon, a hidden gem within an impressive Beaux Arts building tucked away in the exclusive neighbourhood of Beacon Hill. Home to its own outstanding art collection making it a standout in the Boston arts scene. Take some time to settle into this unique boutique hotel, priding itself on oustanding service, with the guest rooms pairing elegance and modern comfort.

Your first experience will take you along the Freedom Trail, on your very own VIP walking tour. An iconic must do whilst in Boston, this private experience will highlight hidden gems and interesting facts steering clear of the crowds, making it a very unique experience. The 2.5-mile road will take you past 16 historically significant sights including the Boston Common, the Massachusetts State House, Granary Burying Ground, arriving at Old North Church for an immersive experience. You will then have time at leisure to explore Boston as you wish. Maybe amble the beautiful Acorn Street, or head to Back Bay and indulge in the independent stores on Newbury Street, along with an impressive range of exquisite restaurants and cafes, not forgetting the iconic lobster roll.  Yoiu can then return to the sanctuary of your hotel for an evening meal, with the main restaurant, The Mooo Steakhouse, providing a range of New England cuisine. Try the Lobster Bisque if you get a chance, finishing with a night cap to round off the evening. 


After a delicious breakfast it’s time to bid farewell  as you leave Boston behind and transfer to your next stop, the beautiful quaint town of Woodstock. Your driver will stop at the picturesque Winslow State Park en route for you to stretch your legs and take in the breathtaking mountain views here. Embark on a loop hike to the summit of Mt. Kearsarge to take in expansive views of the White Mountains, Pleasant Lake, and some of central Vermont’s tallest peaks such as Mt. Sunapee and Ragged Mountain.

Accommodation: XV Beacon ( 2 nights )
Day 3-6

Vermont

Plunge into the heart of Woodstock as you check into its most beautiful address – the Woodstock Inn. The epitome of a grand New England resort, built by the Rockefeller family in the 1960’s, home to heated pools, tennis courts and spa with hot tub nestled in the private walled courtyard. Boasting a prime location, you can head out and browse the unique shops in this beautiful town, like FH Gillingham & Sons general store and the Arts on the Green gallery. Spend time wandering the Main Street with many restaurants and charming boutiques to explore. Heading further afield to the surrounding Green Mountains, an area rich in adventure with its miles of hiking and mountain biking trails. 

The next day we’ve curated a bespoke private tour of Woodstock. Stroll through the iconic village green taking in the town’s unique history and architecture, admiring the restored Georgian, Federal Style and Greek Revival houses as well as local art galleries, and arts and craft stores. You will be given the rare opportunity to take an outside look of the impressive Rockefeller Mansion. Walk Woodstock's beautiful country roads and surrounding farms where you will stop and visit the Billings Farm & Museum, devouring a sublime lunch at the Simon Pearce restaurant. Drive to the Quechee Gorge soaking up the breathtaking view of the valley and Ottauquechee River, its village centre and vintage antique stores. Returning to the wonderful facilities at your hotel for a delicious evening meal in wonderful surroundings. 


Your final experience takes you to a private pottery workshop, where your personal artisan potter will guide you through their fascinating workshop and art collection, demonstrating their exceptional skills and guiding you on the potters wheel, letting you get your hands dirty to create your own masterpiece under their expert eye. 

Accommodation: Woodstock Inn & Resort ( 3 nights )
We design each itinerary around you, so this suggested itinerary is a starting point that we can tweak or transform into something completely bespoke to you.
Call us on 858 523 9000 to start planning your holiday.

Experiences included in this itinerary


Your Hotels


When to visit

  • J
  • F
  • M
  • A
  • M
  • J
  • J
  • A
  • S
  • O
  • N
  • D
Best time to visit
Good time to visit
Average time to visit

Autumn is Boston's most glorious season, though spring and summer are pleasant as well. These times bring in healthy-sized crowds due to favourable weather and special events. Weather usually remains warm throughout September, while cooler temperatures in October bring out the colourful foliage. Winter lasts too long for most people's tastes, stretching from December to April. During this period, visitors can expect temperatures below freezing and plenty of snow.

The best time to visit Vermont is in late spring, summer and early autumn when Fall brings its glorious colours. Most of Vermont is under snow over the winter period and the ski resorts come alive. Cold spells affect Vermont from the end of October till late Spring.

Perfect Pairings: Boston & Vermont
Perfect Pairings: Boston & Vermont

Let's get this Perfect Pairing booked for you. Call us on 858 523 9000 to start planning your trip.

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Why Scott Dunn?

At Scott Dunn, we live and breathe travel. An insatiable appetite to discover the world runs through everything we do. We relish the planning and revel in the detail. We know it’s the smallest touches that make the biggest difference, and we stop at nothing to make every trip not only exceptional but totally unique.

  • Every itinerary is crafted from scratch, based around exactly what’s important to you
  • Packed full of unique experiences, hand-picked by our journeys team
  • Expert local guides enrich your experience in every destination
  • Your own dedicated Travel Specialist who will take care of every detail of your trip
  • We have a 24/7 team providing in-country support and guidance
  • We offer flexibility and financial protection to give you total peace of mind

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